AR102426A1 - INDOLCARBOXAMIDE COMPOUNDS AS BTK INHIBITORS - Google Patents
INDOLCARBOXAMIDE COMPOUNDS AS BTK INHIBITORSInfo
- Publication number
- AR102426A1 AR102426A1 ARP150103454A ARP150103454A AR102426A1 AR 102426 A1 AR102426 A1 AR 102426A1 AR P150103454 A ARP150103454 A AR P150103454A AR P150103454 A ARP150103454 A AR P150103454A AR 102426 A1 AR102426 A1 AR 102426A1
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- alkyl
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- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title 1
- 229940124291 BTK inhibitor Drugs 0.000 title 1
- -1 dichlorotriazinyl Chemical group 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 abstract 1
- 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 abstract 1
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 abstract 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 abstract 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 abstract 1
- 208000019553 vascular disease Diseases 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
También el uso de tales compuestos como inhibidores de la tirosina quinasa de Bruton (Btk) y composiciones farmacéuticas que comprenden tales compuestos. Estos compuestos son de utilidad en el tratamiento, prevención o lentificación de la progresión de enfermedades o trastornos en una variedad de áreas terapéuticas, tales como enfermedades autoinmunes y enfermedad vascular. Reivindicación 1: Un compuesto caracterizado por la fórmula (1), o una de sus sales, en donde: X es CR⁴ o N; A es (i) un resto del grupo de fórmulas (2); (ii) un resto del grupo de fórmulas (3); (iii) un resto del grupo de fórmulas (4); (iv) un resto del grupo de fórmulas (5); (v) un resto del grupo de fórmulas (6); (vi) -CHR⁸(piridinilo) en donde cada piridinilo está sustituido con R⁶ y R⁹; Q¹ es -NR⁷Q², -CR¹⁰R¹⁰NR⁷Q², -C(O)NR⁷(alquilo C₁₋₄ sustituido con cero o 1 R¹¹), -CH=CH₂, -CH=C(CN)S(O)₂CH₃, -S(O)₂CH=CR¹⁰R¹⁰, -NR⁷(diclorotriazinilo), -NR⁷(quinazolin-4-ilo sustituido con cero ó 1 R¹¹), 3-metilenpirrolidin-2-on-1-ilo, o un grupo cíclico seleccionado de 1H-pirrol-2(5H)-on-1-ilo, isoindolin-1-on-2-ilo, quinazolin-4(3H)-on-3-ilo, y quinazolin-2,4(1H,3H)-dion-3-ilo, cada grupo cíclico sustituido con cero a dos sustituyentes seleccionados, de modo independiente, de F, Cl, -CH₃, -CN, y -OCH₃; Q² es -CN, -C(O)(alquilo C₁₋₄ sustituido con cero ó 1 R¹¹), -C(O)(cicloalquilo C₃₋₆ sustituido con cero o 1 R¹¹), -C(O)(cicloalquenilo C₅₋₆), -C(O)CR¹⁰=CR¹⁰R¹⁰, -C(O)C(R¹⁰)=CHCH₂N(CH₃)₂, -C(O)CºCR⁷, -C(O)CºC(hidroxialquilo C₁₋₃), -C(O)CºC(fenilo), -C(O)CºCSi(CH₃)₃, o -S(O)₂CH=CHR¹⁰; R¹ es H, -CH₃, -CF₃, o fenilo sustituido con cero o 1 R¹²; R² es H, -CH₃, ciclopropilo, o fenilo sustituido con cero o 1 R¹², siempre que cero o uno de R¹ y R² es fenilo sustituido con cero o 1 R¹²; R³ es H, F, Cl, I, -CN, o -CH₃; R⁴ es H, F, -OH, -O(alquilo C₁₋₄), -O(alquil C₁₋₄)-O-(alquilo C₁₋₂), -O(CH₂)₁₋₃(fenilo), -O(CH₂)₁₋₃(metoxifenilo), o -O(CH₂)₁₋₃(morfolinilo); R⁵ es H, F, Cl, o -CH₃; R⁶ es H, F, Cl, -CF₃, o alcoxi C₁₋₃; cada R⁶ᵃ es, de modo independiente, H o F; R⁷, en cada aparición, es, de modo independiente, H, alquilo C₁₋₄, o ciclopropilo; R⁸ es H o alquilo C₁₋₄; R⁹ es -CH=CH₂, -CH=CHCH₂N(CH₃)₂, -CºCH, o -CºCCH₃; R¹⁰, en cada aparición, es, de modo independiente, H o -CH₃; R¹¹ es F, Cl, -CN, -CF₃, o alcoxi C₁₋₃; y R¹² es F, Cl, -CN, -CF₃, o alcoxi C₁₋₃.Also the use of such compounds as Bruton tyrosine kinase inhibitors (Btk) and pharmaceutical compositions comprising such compounds. These compounds are useful in the treatment, prevention or slowing of the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease. Claim 1: A compound characterized by the formula (1), or one of its salts, wherein: X is CR⁴ or N; A is (i) a remainder of the group of formulas (2); (ii) a remainder of the group of formulas (3); (iii) a remainder of the group of formulas (4); (iv) a remainder of the group of formulas (5); (v) a remainder of the group of formulas (6); (vi) -CHR⁸ (pyridinyl) wherein each pyridinyl is substituted with R⁶ and R⁹; Q¹ is -NR⁷Q², -CR¹⁰R¹⁰NR⁷Q², -C (O) NR⁷ (C alquilo alkyl substituted with zero or 1 R¹¹), -CH = CH₂, -CH = C (CN) S (O) ₂CH₃, -S (O) ₂CH = CR¹⁰R¹⁰, -NR⁷ (dichlorotriazinyl), -NR⁷ (quinazolin-4-yl substituted with zero or 1 R¹¹), 3-methylene pyrrolidin-2-on-1-yl, or a cyclic group selected from 1H-pyrrole-2 ( 5H) -on-1-yl, isoindolin-1-on-2-yl, quinazolin-4 (3H) -on-3-yl, and quinazolin-2,4 (1H, 3H) -dion-3-yl, each cyclic group substituted with zero to two substituents independently selected from F, Cl, -CH₃, -CN, and -OCH₃; Q² is -CN, -C (O) (C₁₋₄ alkyl substituted with zero or 1 R¹¹), -C (O) (C₃₋₆ cycloalkyl substituted with zero or 1 R¹¹), -C (O) (C₅₋ cycloalkenyl ₆), -C (O) CR¹⁰ = CR¹⁰R¹⁰, -C (O) C (R¹⁰) = CHCH₂N (CH₃) ₂, -C (O) CºCR⁷, -C (O) CºC (hydroxyalkyl C₁₋₃), -C (O) C ° C (phenyl), -C (O) C ° C Si (CH₃) ₃, or -S (O) ₂CH = CHR¹⁰; R¹ is H, -CH₃, -CF₃, or phenyl substituted with zero or 1 R¹²; R² is H, -CH₃, cyclopropyl, or phenyl substituted with zero or 1 R¹², provided that zero or one of R¹ and R² is phenyl substituted with zero or 1 R¹²; R³ is H, F, Cl, I, -CN, or -CH₃; R⁴ is H, F, -OH, -O (C₁₋₄ alkyl), -O (C₁₋₄ alkyl) -O- (C₁₋₂ alkyl), -O (CH₂) ₁₋₃ (phenyl), -O (CH₂) ₁₋₃ (methoxyphenyl), or -O (CH₂) ₁₋₃ (morpholinyl); R⁵ is H, F, Cl, or -CH₃; R⁶ is H, F, Cl, -CF₃, or C₁₋₃ alkoxy; each R⁶ᵃ is, independently, H or F; R⁷, at each occurrence, is, independently, H, C₁₋₄ alkyl, or cyclopropyl; R⁸ is H or C₁₋₄ alkyl; R⁹ is -CH = CH₂, -CH = CHCH₂N (CH₃) ₂, -CºCH, or -CºCCH₃; R¹⁰, at each occurrence, is, independently, H or -CH₃; R¹¹ is F, Cl, -CN, -CF₃, or C₁₋₃ alkoxy; and R¹² is F, Cl, -CN, -CF₃, or C₁₋₃ alkoxy.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US201462068225P | 2014-10-24 | 2014-10-24 |
Publications (1)
Publication Number | Publication Date |
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AR102426A1 true AR102426A1 (en) | 2017-03-01 |
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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ARP150103454A AR102426A1 (en) | 2014-10-24 | 2015-10-23 | INDOLCARBOXAMIDE COMPOUNDS AS BTK INHIBITORS |
ARP200102971A AR120317A2 (en) | 2014-10-24 | 2020-10-27 | INDOLCARBOXAMIDE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND SUCH COMPOUNDS FOR USE IN THE TREATMENT OF AUTOIMMUNE DISEASE OR CHRONIC INFLAMMATORY DISEASE |
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Application Number | Title | Priority Date | Filing Date |
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ARP200102971A AR120317A2 (en) | 2014-10-24 | 2020-10-27 | INDOLCARBOXAMIDE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND SUCH COMPOUNDS FOR USE IN THE TREATMENT OF AUTOIMMUNE DISEASE OR CHRONIC INFLAMMATORY DISEASE |
Country Status (34)
Country | Link |
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US (8) | US9688629B2 (en) |
EP (2) | EP3461821B1 (en) |
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